(E,E)-farnesol

all-(E)-farnesol

CAS: 106-28-5 C15 H26 O MW: 222.37142000 floral

Identification

Name(E,E)-farnesol
IUPAC(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
CAS Number106-28-5
FDA UNIIX23PI60R17
Molecular FormulaC15 H26 O
Molecular Weight222.37142000
MDL NumberMFCD00002918
Nikkaji NumberJ5.049K
Beilstein1763926

Regulatory

Physical Properties

Appearance colorless clear liquid (est)
Assay 97.00 to 100.00 sum of isomers
Food Chemicals Codex Listed No
Specific Gravity 0.88400 to 0.88900 @ 25.00 °C.
Pounds per Gallon - (est). 7.356 to 7.397
Refractive Index 1.48700 to 1.49400 @ 20.00 °C.
Boiling Point 283.00 to 284.00 °C. @ 760.00 mm Hg, 137.00 °C. @ 3.00 mm Hg
Vapor Pressure 0.000370 mmHg @ 25.00 °C. (est)
Vapor Density >1 ( Air = 1 )
Flash Point 230.00 °F. TCC ( 110.00 °C. )
logP (o/w) 5.314 (est)
Soluble in alcohol
Insoluble in water

Organoleptic Properties

Odor Strength low
Odor Description
at 100.00 %.
subtle, green, floral
Taste Description green

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 6000 mg/kg
Dermal Toxicityskin-rabbit LD50 > 5000 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
IFRA Critical EffectSensitization
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%)Category 1: Products applied to the lips
NotesIFRA FLAVOR REQUIREMENTS:
Recommendation for (E,E)-farnesol flavor usage levels up to2.0000 ppm in the finished product.

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Potential Uses

FR aldehydic FR floral FR lily FR lily of the valley waxy

Natural Occurrence

ambrette seed concrete @ 2.16% Data ambrette seed oil @ 3.50% Data boronia absolute @ 0.08% Data cabocla flower oil brazil @ 0.50% Data champaca concrete @ 0.20% Data cinnamon ceylon cinnamon leaf clove bud oil @ 1.08% Data clove leaf oil @ 0.61% Data clove stem oil india @ 0.69% Data couroupita guianensis aubl. flower oil brazil @ 16.10% Data curry fruit oil india @ <0.05% Data curry leaf oil india @ 0.20% Data geranium rose-scented oil (pelargonium spp.) cuba @ 0.20% Data ginger root oil CO2 extract @ 0.88% Data guava leaf oil cuba @ 0.20% Data jasmin absolute china (from concrete) @ 0.09% Data jasmin sambac absolute egypt @ 1.30% Data palmarosa oil @ 1.90% Data rose oil otto bulgaria @ 1.98% Data skimmia laureola oil @ 0.7% Data thevetia peruviana (pers.) k. schum. flower oil brazil @ 0.10% Data ylang ylang oil @ 0.84% Data ylang ylang oil CO2 extract @ 1.39% Data

Synonyms

2,6- di-trans-farnesol 2,6,10- dodecatrien-1-ol, 3,7,11-trimethyl-, (2E,6E)- 2,6,10- dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)- (2-trans,6-trans)- farnesol (2E,6E)- farnesol (E,E)-2,6- farnesol (E)- farnesol 2-trans,6-trans- farnesol all-(E)- farnesol all-trans- farnesol trans, trans- farnesol trans,trans- farnesol (2E,6E)-3,7,11- trimethyl-1-dodeca-2,6,10-trienol (2E,6E)-3,7,11- trimethyl-2,6,10-dodecatrien-1-ol (E,E)-3,7,11- trimethyl-2,6,10-dodecatrien-1-ol trans,trans-3,7,11- trimethyl-2,6,10-dodecatrien-1-ol (2E,6E)-3,7,11- trimethyl-dodeca-2,6,10-trien-1-ol 3,7,11- trimethyldodeca-2-trans,6-trans,10-trien-1-ol (2-trans,6-trans)-3,7,11- trimethyldodeca-2,6,10-trien-1-ol (2E,6E)-3,7,11- trimethyldodeca-2,6,10-trien-1-ol Info: Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.) PubMed: Changes in volatile compound composition of Antrodia camphorata during solid state fermentation. PubMed: Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka). PubMed: Essential oil composition and antimicrobial activities of two closely related species, Alpinia mutica Roxb. and Alpinia latilabris Ridl., from Peninsular Malaysia. PubMed: Gold(I) as an artificial cyclase: short stereodivergent syntheses of (-)-epiglobulol and (-)-4β,7α- and (-)-4α,7α-aromadendranediols. PubMed: Assessment of the antioxidant and antiproliferative effects of sesquiterpenic compounds in in vitro Caco-2 cell models. PubMed: [Tobacco--once a medicinal plant. Does it contain substances with medicinal properties?]. PubMed: Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach. PubMed: Chemical composition and in vitro antimicrobial and antioxidant activities of Citrus aurantium l. flowers essential oil (Neroli oil). PubMed: Characterization of essential oil from Citrus aurantium L. flowers: antimicrobial and antioxidant activities. PubMed: Determination of E,E-farnesol in Makgeolli (rice wine) using dynamic headspace sampling and stir bar sorptive extraction coupled with gas chromatography-mass spectrometry. PubMed: Study of trans-trans farnesol effect on hyphae formation by Yarrowia lipolytica. PubMed: β-ionone induces cell cycle arrest and apoptosis in human prostate tumor cells. PubMed: Engineered heterologous FPP synthases-mediated Z,E-FPP synthesis in E. coli. PubMed: Chemical composition and antifungal activity of Matricaria recutita flower essential oil against medically important dermatophytes and soil-borne pathogens. PubMed: Specific involvement of two amino acid residues in cis-nerolidol binding to odorant-binding protein 5 AlinOBP5 in the alfalfa plant bug, Adelphocoris lineolatus (Goeze). PubMed: A convergent stereocontrolled total synthesis of (-)-terpestacin. PubMed: Comparative study of the chemical composition and biological activities of Magnolia grandiflora and Magnolia virginiana flower essential oils. PubMed: Quorum sensing activity in Ophiostoma ulmi: effects of fusel oils and branched chain amino acids on yeast-mycelial dimorphism. PubMed: Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis). PubMed: Effect of exogenous administration of Candida albicans autoregulatory alcohols in a murine model of hematogenously disseminated candidiasis. PubMed: Changes in volatile compound composition of Antrodia camphorata during solid state fermentation. PubMed: Drimenol: A versatile synthon for compounds with trans-drimane skeleton. PubMed: Influences of trans-trans farnesol, a membrane-targeting sesquiterpenoid, on Streptococcus mutans physiology and survival within mixed-species oral biofilms. PubMed: Evaluation of the mutagenicity of sesquiterpenic compounds and their influence on the susceptibility towards antibiotics of two clinically relevant bacterial strains. PubMed: Application of a multidimensional gas chromatography system with simultaneous mass spectrometric and flame ionization detection to the analysis of sandalwood oil. PubMed: Variation in volatile leaf oils of eleven eucalyptus species harvested from korbous arboreta (Tunisia). PubMed: The quorum-sensing molecule E,E-farnesol--its variable secretion and its impact on the growth and metabolism of Candida species. PubMed: Candida species extracellular alcohols: production and effect in sessile cells. PubMed: Production of geranylgeraniol on overexpression of a prenyl diphosphate synthase fusion gene in Saccharomyces cerevisiae. PubMed: Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem. PubMed: Determination of the volatile composition in essential oil of Descurainia sophia (L.) Webb ex Prantl (Flixweed) by gas chromatography/mass spectrometry (GC/MS). PubMed: Recovery of E,E-farnesol from cultures of yeast erg9 mutants: extraction with polymeric beads and purification by normal-phase chromatography. PubMed: Flowerhead volatile oil composition of soilless culture-grown Chrysanthemum balsamita L. PubMed: Quantification approach for assessment of sparkling wine volatiles from different soils, ripening stages, and varieties by stir bar sorptive extraction with liquid desorption. PubMed: Overexpression of the gene encoding HMG-CoA reductase in Saccharomyces cerevisiae for production of prenyl alcohols. PubMed: Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography-quadrupole mass spectrometry for the determination of volatile compounds in wines. PubMed: Synthesis of cordiaquinones B, C, J, and K on the basis of a bioinspired approach and the revision of the relative stereochemistry of cordiaquinone C. PubMed: Secretion of E,E-farnesol and biofilm formation in eight different Candida species. PubMed: Morphogenesis control in Candida albicans and Candida dubliniensis through signaling molecules produced by planktonic and biofilm cells. PubMed: Characterization of (E,E)-farnesol and its fatty acid esters from anal scent glands of nutria (Myocastor coypus) by gas chromatography-mass spectrometry and gas chromatography-infrared spectrometry. PubMed: The rice (E)-beta-caryophyllene synthase (OsTPS3) accounts for the major inducible volatile sesquiterpenes. PubMed: Analysis of the essential oil of Grindelia discoidea. PubMed: Zoledronate inhibits endothelial cell adhesion, migration and survival through the suppression of multiple, prenylation-dependent signaling pathways. PubMed: Structure of the human mitochondrial monoamine oxidase B: new chemical implications for neuroprotectant drug design. PubMed: Determination of terpenes in tequila by solid phase microextraction-gas chromatography-mass spectrometry. PubMed: A soluble form of phosphatase in Saccharomyces cerevisiae capable of converting farnesyl diphosphate into E,E-farnesol. PubMed: Isolation and characterization of a monoamine oxidase B selective inhibitor from tobacco smoke. PubMed: Volatile constituents of redblush grapefruit (Citrus paradisi) and pummelo (Citrus grandis) peel essential oils from Kenya. PubMed: Monitoring farnesol-induced toxicity in tobacco BY-2 cells with a fluorescent analog. PubMed: Farnesol concentrations required to block germ tube formation in Candida albicans in the presence and absence of serum. PubMed: Responses to sex pheromone and plant odours by olfactory receptor neurons housed in sensilla auricillica of the codling moth, Cydia pomonella (Lepidoptera: Tortricidae). PubMed: Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors. PubMed: Comprehensive two-dimensional gas chromatography with flame ionization and time-of-flight mass spectrometry detection: qualitative and quantitative analysis of West Australian sandalwood oil. PubMed: Farnesol-DMPC phase behaviour: a (2)H-NMR study. PubMed: Quorum sensing in Candida albicans: probing farnesol's mode of action with 40 natural and synthetic farnesol analogs. PubMed: Detection of farnesyl diphosphate accumulation in yeast ERG9 mutants. PubMed: The maize gene terpene synthase 1 encodes a sesquiterpene synthase catalyzing the formation of (E)-beta-farnesene, (E)-nerolidol, and (E,E)-farnesol after herbivore damage. PubMed: Squalestatin 1-inducible expression of rat CYP2B: evidence that an endogenous isoprenoid is an activator of the constitutive androstane receptor. PubMed: African elephant sesquiterpenes. II. Identification and synthesis of new derivatives of 2,3-dihydrofarnesol. PubMed: Alendronate inhibits invasion of PC-3 prostate cancer cells by affecting the mevalonate pathway. PubMed: Quorum sensing in the dimorphic fungus Candida albicans is mediated by farnesol. PubMed: Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka). PubMed: Metabolism of farnesyl diphosphate in tobacco BY-2 cells treated with squalestatin. PubMed: Synthesis and biological evaluation of the geometric farnesylated analogues of the a-factor mating peptide of Saccharomyces cerevisiae. PubMed: Effects of statins on vascular wall: vasomotor function, inflammation, and plaque stability. PubMed: Sex pheromone mimicry in the early spider orchid (ophrys sphegodes): patterns of hydrocarbons as the key mechanism for pollination by sexual deception. PubMed: Farnesyl anthranilate suppresses the growth, in vitro and in vivo, of murine B16 melanomas. PubMed: Pleiotropic effects of statins in atherosclerosis and diabetes. PubMed: Comparison of headspace techniques for sampling volatile natural products in a dynamic system. PubMed: Direct vascular effects of HMG-CoA reductase inhibitors. PubMed: Studies on the Synthesis of Elegan-Type Linear Diterpenes: The Efficient Total Syntheses of Eleganolone, Eleganolone Acetate, Elegandiol, Eleganonal, and Epoxyeleganolone PubMed: Lovastatin induces apoptosis by inhibiting mitotic and post-mitotic events in cultured mesangial cells. PubMed: Activators of the nuclear hormone receptors PPARalpha and FXR accelerate the development of the fetal epidermal permeability barrier. PubMed: Pharmacological control of the mevalonate pathway: effect on arterial smooth muscle cell proliferation. PubMed: Male sex pheromone of a giant danaine butterfly,Idea leuconoe. PubMed: Identification and characterization of geranylgeraniol kinase and geranylgeranyl phosphate kinase from the Archaebacterium Sulfolobus acidocaldarius. PubMed: Effects of farnesol on the thermotropic behavior of dimyristoylphosphatidylcholine. PubMed: Directed cell killing (apoptosis) in human lymphoblastoid cells incubated in the presence of farnesol: effect of phosphatidylcholine. PubMed: Differences in sensitivity to farnesol toxicity between neoplastically- and non-neoplastically-derived cells in culture. PubMed: Requirement for isoprenoid-dependent posttranslational modifications in the cell-cycle progression of human breast-cancer cells. PubMed: Growth inhibition of leukemia cell line CEM-C1 by farnesol: effects of phosphatidylcholine and diacylglycerol. PubMed: Chemical analysis of temporal gland secretions collected from an Asian bull elephant during a four-month musth episode. PubMed: The conformation of dolichol. PubMed: Chemosensory responses in two species of elephants to constituents of temporal gland secretion and musth urine. PubMed: Odor mimetism? : Key substances inOphrys lutea-Andrena pollination relationship (Orchidaceae: Andrenidae). PubMed: Total synthesis of chain-length-uniform dolichyl phosphates and their fitness to accept hexoses in the enzymatic formation of lipoglycans. PubMed: Constituents of temporal gland secretion of the African elephant,Loxodonta africana. PubMed: The Nasonov pheromone of the honeybeeApis mellifera L. (Hymenoptera, Apidae). Part II. Bioassay of the components using foragers. PubMed: Photosynthetic pigments of green sulfur bacteria. The esterifying alcohols of bacteriochlorophylls c from Chlorobium limicola. PubMed: Levels of short-chain fatty acids and of abscisic acid in water-stressed and non-stressed leaves and their effects on stomata in epidermal strips and excised leaves. PubMed: Hydrolysis and isomerization of trans,trans-farnesyl diphosphate by Andrographis tissue-culture enzymes. PubMed: Comparison between Biosynthesis of ent-Kaurene in Germinating Tomato Seeds and Cell Suspension Cultures of Tomato and Tobacco. PubMed: Detection and preliminary identification of endogenous antitranspirants in water-stressed Sorghum plants. PubMed: Biosynthesis of trans, trans- and cis, trans-farnesols by soluble enzymes from tissue cultures of Andrographis paniculata. PubMed: All-trans-farnesol: a naturally occurring antitranspirant? PubMed: Synthesis of cecropia juvenile hormone from trans,trans-farnesol. PubMed: Lipid metabolism in helminth parasites--VI. Synthesis of 2-cis,6-trans farnesol by Hymenolepis diminuta (Cestoda).